SharpesTriumph
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I've seen people mentioning getting a better return in February, but I struggle to see that happening. $$ matching would become more difficult and we wouldn't have the benefit of the expanded roster limits of the offseason. Any sort of 5-1 trade means we're waiving 3 or 4 people off o our current roster in order to get that deal done.
Yeah ideally the Blazers would get a deal done before media day and training camp. Yes its harder to do a deal with hard roster limits. It will be awkward for the young players on the roster, and just awkward for everyone associated with the team from front office to owners to business to ticket sales.
That said the Blazers don't HAVE to do a Dame deal prior. Many more players will be eligible to be traded after Dec 15th; which will make both the salary matching easier as well as open up new possibilities of players being sent to Portland in return. Some teams situation might change and they prefer to increase an offer for Lillard. However its possible a team, even Miami, will find themselves with a changed situation such as a Bam/Butler injury and not want to do a trade during the season they would do now. If Dame plays its possible he gets injured, if he doesn't play it might raise more concerns about his buy in to a new situation as well as long term value.
I'd probably pull the trigger on a deal if we are getting decent value back such as all the picks/swaps/Herro/Martin/Jaquez/Jovic that Miami can offer. I put more value into those unprotected picks and swaps than most fans here though. But I wouldn't give Dame away for a significantly lesser return - in that case just wait to see whats available later. Yes theres some risk a later trade won't be better; but with a poor return now that risk is pretty low and worth taking a chance on for a possible better return in the season.